NPASS Compound

Structure

NPC472478 OpenBabel07101718292D 22 25 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 6 16 2 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 5 1 1 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	329.921
LogP:	2.683
LogD:	2.074
LogS:	-4.001
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	5.809
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.648422949074302e-05
Pgp-inhibitor:	0.169
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	92.9087142944336%
Volume Distribution (VD):	1.368
Pgp-substrate:	4.934729099273682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.592

ADMET: Excretion

Clearance (CL):	4.186
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.373
Rat Oral Acute Toxicity:	0.501
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.385
Carcinogencity:	0.751
Eye Corrosion:	0.019
Eye Irritation:	0.152
Respiratory Toxicity:	0.968

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC472478

Natural Product ID:	NPC472478
*Common Name:**	OPSDBQPQYGWZJL-UYUBTLJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OPSDBQPQYGWZJL-UYUBTLJZSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13-14-5-6-16-19(3)9-4-8-18(2,12-21)15(19)7-10-20(16,11-14)17(13)22/h6,14-15,21H,1,4-5,7-12H2,2-3H3/t14-,15-,18-,19-,20-/m1/s1
SMILES:	CC1(CCCC2(C1CCC34C2=CCC(C3)C(=C)C4=O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426486
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	=	14500.0	nM	PMID[469780]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	11200.0	nM	PMID[469780]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	13800.0	nM	PMID[469780]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	31000.0	nM	PMID[469780]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	16300.0	nM	PMID[469780]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	32000.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22300.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17700.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4700.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9800.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20300.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14000.0	nM	PMID[469780]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21500.0	nM	PMID[469780]
NPT27	Others	Unspecified		IC50	=	39300.0	nM	PMID[469780]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC472478 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1007
0.2-0.3	5644
0.3-0.4	15578
0.4-0.5	7113
0.5-0.6	6536
0.6-0.7	4315
0.7-0.8	2026
0.8-0.85	239
0.85-0.9	70
0.9-0.95	26
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC472490
0.9241	High Similarity	NPC214043
0.9241	High Similarity	NPC85774
0.9241	High Similarity	NPC237712
0.9136	High Similarity	NPC93778
0.9125	High Similarity	NPC469948
0.9079	High Similarity	NPC106078
0.9012	High Similarity	NPC474778
0.9012	High Similarity	NPC474733
0.9012	High Similarity	NPC145879
0.9012	High Similarity	NPC474732
0.9012	High Similarity	NPC31564
0.9	High Similarity	NPC59453
0.9	High Similarity	NPC221758
0.9	High Similarity	NPC227064
0.9	High Similarity	NPC58841
0.9	High Similarity	NPC321187
0.9	High Similarity	NPC82902
0.9	High Similarity	NPC473246
0.9	High Similarity	NPC329043
0.9	High Similarity	NPC161423
0.8987	High Similarity	NPC151519
0.8974	High Similarity	NPC2482
0.8961	High Similarity	NPC82635
0.8902	High Similarity	NPC58063
0.8902	High Similarity	NPC475740
0.8889	High Similarity	NPC474218
0.8889	High Similarity	NPC471224
0.8861	High Similarity	NPC116797
0.8861	High Similarity	NPC121984
0.8795	High Similarity	NPC328539
0.878	High Similarity	NPC222613
0.878	High Similarity	NPC51014
0.878	High Similarity	NPC469994
0.878	High Similarity	NPC475022
0.878	High Similarity	NPC118648
0.878	High Similarity	NPC473168
0.878	High Similarity	NPC327115
0.8765	High Similarity	NPC472265
0.875	High Similarity	NPC193347
0.875	High Similarity	NPC320514
0.8706	High Similarity	NPC272746
0.869	High Similarity	NPC119416
0.869	High Similarity	NPC309603
0.869	High Similarity	NPC1015
0.869	High Similarity	NPC472477
0.869	High Similarity	NPC31985
0.869	High Similarity	NPC326627
0.869	High Similarity	NPC186688
0.869	High Similarity	NPC472475
0.869	High Similarity	NPC477943
0.869	High Similarity	NPC310010
0.869	High Similarity	NPC26959
0.869	High Similarity	NPC473999
0.869	High Similarity	NPC268406
0.8675	High Similarity	NPC96496
0.8675	High Similarity	NPC317590
0.8675	High Similarity	NPC90652
0.8675	High Similarity	NPC136548
0.8659	High Similarity	NPC29447
0.8659	High Similarity	NPC470574
0.8659	High Similarity	NPC476426
0.8659	High Similarity	NPC474083
0.8625	High Similarity	NPC147066
0.8625	High Similarity	NPC3915
0.8608	High Similarity	NPC215843
0.8608	High Similarity	NPC474113
0.8605	High Similarity	NPC474807
0.8605	High Similarity	NPC474736
0.8588	High Similarity	NPC48010
0.8588	High Similarity	NPC191684
0.8588	High Similarity	NPC126993
0.8588	High Similarity	NPC85173
0.8571	High Similarity	NPC471722
0.8571	High Similarity	NPC471724
0.8571	High Similarity	NPC328313
0.8571	High Similarity	NPC470417
0.8554	High Similarity	NPC20688
0.8554	High Similarity	NPC72133
0.8554	High Similarity	NPC155011
0.8537	High Similarity	NPC144258
0.8537	High Similarity	NPC33913
0.8537	High Similarity	NPC476412
0.8519	High Similarity	NPC103486
0.8519	High Similarity	NPC310989
0.85	High Similarity	NPC476809
0.8488	Intermediate Similarity	NPC473998
0.8488	Intermediate Similarity	NPC475806
0.8488	Intermediate Similarity	NPC185936
0.8488	Intermediate Similarity	NPC168027
0.8488	Intermediate Similarity	NPC131872
0.8481	Intermediate Similarity	NPC62336
0.8481	Intermediate Similarity	NPC189485
0.8471	Intermediate Similarity	NPC275740
0.8471	Intermediate Similarity	NPC32830
0.8471	Intermediate Similarity	NPC2983
0.8471	Intermediate Similarity	NPC86319
0.8471	Intermediate Similarity	NPC474245
0.8471	Intermediate Similarity	NPC76879
0.8462	Intermediate Similarity	NPC470525
0.8462	Intermediate Similarity	NPC263582
0.8452	Intermediate Similarity	NPC142361
0.8452	Intermediate Similarity	NPC472481
0.8452	Intermediate Similarity	NPC474684
0.8452	Intermediate Similarity	NPC472482
0.8452	Intermediate Similarity	NPC472484
0.8415	Intermediate Similarity	NPC175410
0.8415	Intermediate Similarity	NPC471036
0.8415	Intermediate Similarity	NPC307258
0.8415	Intermediate Similarity	NPC476082
0.8415	Intermediate Similarity	NPC118800
0.8415	Intermediate Similarity	NPC278648
0.8415	Intermediate Similarity	NPC291320
0.8395	Intermediate Similarity	NPC14151
0.8395	Intermediate Similarity	NPC278459
0.8395	Intermediate Similarity	NPC38350
0.8395	Intermediate Similarity	NPC201912
0.8395	Intermediate Similarity	NPC6434
0.8395	Intermediate Similarity	NPC477372
0.8391	Intermediate Similarity	NPC475255
0.8391	Intermediate Similarity	NPC109305
0.8391	Intermediate Similarity	NPC233118
0.8391	Intermediate Similarity	NPC250575
0.8375	Intermediate Similarity	NPC477371
0.8375	Intermediate Similarity	NPC7232
0.8375	Intermediate Similarity	NPC201459
0.8372	Intermediate Similarity	NPC129913
0.8372	Intermediate Similarity	NPC171441
0.8372	Intermediate Similarity	NPC320026
0.8372	Intermediate Similarity	NPC472476
0.8354	Intermediate Similarity	NPC325946
0.8354	Intermediate Similarity	NPC197659
0.8354	Intermediate Similarity	NPC471035
0.8354	Intermediate Similarity	NPC165711
0.8354	Intermediate Similarity	NPC212661
0.8353	Intermediate Similarity	NPC143767
0.8353	Intermediate Similarity	NPC474677
0.8353	Intermediate Similarity	NPC193360
0.8353	Intermediate Similarity	NPC53911
0.8353	Intermediate Similarity	NPC131470
0.8333	Intermediate Similarity	NPC94666
0.8333	Intermediate Similarity	NPC472479
0.8333	Intermediate Similarity	NPC89077
0.8333	Intermediate Similarity	NPC94755
0.8333	Intermediate Similarity	NPC194417
0.8313	Intermediate Similarity	NPC165064
0.8313	Intermediate Similarity	NPC180834
0.8313	Intermediate Similarity	NPC146683
0.8312	Intermediate Similarity	NPC303613
0.8312	Intermediate Similarity	NPC474228
0.8295	Intermediate Similarity	NPC8993
0.8295	Intermediate Similarity	NPC111015
0.8295	Intermediate Similarity	NPC245972
0.8295	Intermediate Similarity	NPC196485
0.8293	Intermediate Similarity	NPC260956
0.8293	Intermediate Similarity	NPC48362
0.8293	Intermediate Similarity	NPC212083
0.8289	Intermediate Similarity	NPC265782
0.8289	Intermediate Similarity	NPC2634
0.8289	Intermediate Similarity	NPC251929
0.8289	Intermediate Similarity	NPC307176
0.8276	Intermediate Similarity	NPC19114
0.8276	Intermediate Similarity	NPC262870
0.8276	Intermediate Similarity	NPC154101
0.8272	Intermediate Similarity	NPC108955
0.8272	Intermediate Similarity	NPC45495
0.8256	Intermediate Similarity	NPC472489
0.8256	Intermediate Similarity	NPC477973
0.8256	Intermediate Similarity	NPC184663
0.8256	Intermediate Similarity	NPC475921
0.8256	Intermediate Similarity	NPC474570
0.8256	Intermediate Similarity	NPC262043
0.8256	Intermediate Similarity	NPC474704
0.825	Intermediate Similarity	NPC469996
0.825	Intermediate Similarity	NPC475994
0.8235	Intermediate Similarity	NPC233836
0.8235	Intermediate Similarity	NPC187376
0.8235	Intermediate Similarity	NPC159046
0.8235	Intermediate Similarity	NPC141292
0.8235	Intermediate Similarity	NPC136948
0.8228	Intermediate Similarity	NPC180886
0.8222	Intermediate Similarity	NPC108078
0.8214	Intermediate Similarity	NPC190704
0.8214	Intermediate Similarity	NPC133954
0.8214	Intermediate Similarity	NPC102292
0.8214	Intermediate Similarity	NPC471034
0.8214	Intermediate Similarity	NPC6185
0.8214	Intermediate Similarity	NPC274724
0.8214	Intermediate Similarity	NPC76518
0.8214	Intermediate Similarity	NPC202868
0.8214	Intermediate Similarity	NPC241512
0.8205	Intermediate Similarity	NPC241854
0.8205	Intermediate Similarity	NPC251970
0.8205	Intermediate Similarity	NPC476046
0.8202	Intermediate Similarity	NPC476174
0.8202	Intermediate Similarity	NPC271195
0.8193	Intermediate Similarity	NPC470015
0.8193	Intermediate Similarity	NPC470165
0.8193	Intermediate Similarity	NPC69279
0.8193	Intermediate Similarity	NPC470046

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC472478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1334
0.2-0.3	4122
0.3-0.4	2498
0.4-0.5	581
0.5-0.6	173
0.6-0.7	117
0.7-0.8	134
0.8-0.85	42
0.85-0.9	8
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD3665	Phase 1
0.9	High Similarity	NPD4786	Approved
0.9	High Similarity	NPD3133	Approved
0.9	High Similarity	NPD3666	Approved
0.8987	High Similarity	NPD3667	Approved
0.878	High Similarity	NPD3618	Phase 1
0.875	High Similarity	NPD4223	Phase 3
0.875	High Similarity	NPD4221	Approved
0.8706	High Similarity	NPD6079	Approved
0.869	High Similarity	NPD4753	Phase 2
0.869	High Similarity	NPD5328	Approved
0.8554	High Similarity	NPD5279	Phase 3
0.8537	High Similarity	NPD4197	Approved
0.8434	Intermediate Similarity	NPD5329	Approved
0.8415	Intermediate Similarity	NPD4788	Approved
0.8409	Intermediate Similarity	NPD4629	Approved
0.8409	Intermediate Similarity	NPD5210	Approved
0.8391	Intermediate Similarity	NPD4202	Approved
0.8333	Intermediate Similarity	NPD5205	Approved
0.8333	Intermediate Similarity	NPD4693	Phase 3
0.8333	Intermediate Similarity	NPD4688	Approved
0.8333	Intermediate Similarity	NPD4689	Approved
0.8333	Intermediate Similarity	NPD5690	Phase 2
0.8333	Intermediate Similarity	NPD4138	Approved
0.8333	Intermediate Similarity	NPD4690	Approved
0.8315	Intermediate Similarity	NPD5221	Approved
0.8315	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD5222	Approved
0.8289	Intermediate Similarity	NPD4747	Approved
0.8289	Intermediate Similarity	NPD4691	Approved
0.8272	Intermediate Similarity	NPD4695	Discontinued
0.825	Intermediate Similarity	NPD3617	Approved
0.8222	Intermediate Similarity	NPD5173	Approved
0.8158	Intermediate Similarity	NPD4137	Phase 3
0.8148	Intermediate Similarity	NPD4195	Approved
0.8118	Intermediate Similarity	NPD5280	Approved
0.8118	Intermediate Similarity	NPD4694	Approved
0.8118	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD4697	Phase 3
0.8095	Intermediate Similarity	NPD3668	Phase 3
0.8043	Intermediate Similarity	NPD5286	Approved
0.8043	Intermediate Similarity	NPD4696	Approved
0.8043	Intermediate Similarity	NPD5285	Approved
0.8022	Intermediate Similarity	NPD6084	Phase 2
0.8022	Intermediate Similarity	NPD6083	Phase 2
0.8022	Intermediate Similarity	NPD4755	Approved
0.7978	Intermediate Similarity	NPD6399	Phase 3
0.7975	Intermediate Similarity	NPD4058	Approved
0.7957	Intermediate Similarity	NPD5223	Approved
0.7931	Intermediate Similarity	NPD5737	Approved
0.7931	Intermediate Similarity	NPD6672	Approved
0.7907	Intermediate Similarity	NPD5330	Approved
0.7907	Intermediate Similarity	NPD4519	Discontinued
0.7907	Intermediate Similarity	NPD4623	Approved
0.7907	Intermediate Similarity	NPD7334	Approved
0.7907	Intermediate Similarity	NPD7521	Approved
0.7907	Intermediate Similarity	NPD6409	Approved
0.7907	Intermediate Similarity	NPD7146	Approved
0.7907	Intermediate Similarity	NPD6684	Approved
0.7875	Intermediate Similarity	NPD7339	Approved
0.7875	Intermediate Similarity	NPD6942	Approved
0.7872	Intermediate Similarity	NPD5225	Approved
0.7872	Intermediate Similarity	NPD5226	Approved
0.7872	Intermediate Similarity	NPD5211	Phase 2
0.7872	Intermediate Similarity	NPD4633	Approved
0.7872	Intermediate Similarity	NPD5224	Approved
0.7865	Intermediate Similarity	NPD7515	Phase 2
0.7849	Intermediate Similarity	NPD4700	Approved
0.7802	Intermediate Similarity	NPD5695	Phase 3
0.7792	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5175	Approved
0.7789	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5733	Approved
0.775	Intermediate Similarity	NPD4687	Approved
0.7742	Intermediate Similarity	NPD5696	Approved
0.7738	Intermediate Similarity	NPD4692	Approved
0.7738	Intermediate Similarity	NPD4139	Approved
0.7727	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6903	Approved
0.7722	Intermediate Similarity	NPD5276	Approved
0.7708	Intermediate Similarity	NPD5141	Approved
0.7667	Intermediate Similarity	NPD5284	Approved
0.7667	Intermediate Similarity	NPD5281	Approved
0.7632	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4754	Approved
0.7586	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4096	Approved
0.7551	Intermediate Similarity	NPD5697	Approved
0.7528	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD4243	Approved
0.7475	Intermediate Similarity	NPD6011	Approved
0.7475	Intermediate Similarity	NPD5168	Approved
0.7475	Intermediate Similarity	NPD6881	Approved
0.7475	Intermediate Similarity	NPD6899	Approved
0.7475	Intermediate Similarity	NPD4729	Approved
0.7475	Intermediate Similarity	NPD5128	Approved
0.7475	Intermediate Similarity	NPD4730	Approved
0.7449	Intermediate Similarity	NPD6402	Approved
0.7449	Intermediate Similarity	NPD4768	Approved
0.7449	Intermediate Similarity	NPD5739	Approved
0.7449	Intermediate Similarity	NPD6675	Approved
0.7449	Intermediate Similarity	NPD7128	Approved
0.7449	Intermediate Similarity	NPD4767	Approved
0.7444	Intermediate Similarity	NPD6673	Approved
0.7444	Intermediate Similarity	NPD6080	Approved
0.7444	Intermediate Similarity	NPD6904	Approved
0.7412	Intermediate Similarity	NPD7525	Registered
0.74	Intermediate Similarity	NPD6014	Approved
0.74	Intermediate Similarity	NPD6013	Approved
0.74	Intermediate Similarity	NPD6012	Approved
0.7391	Intermediate Similarity	NPD5133	Approved
0.7375	Intermediate Similarity	NPD4789	Approved
0.7374	Intermediate Similarity	NPD5701	Approved
0.7333	Intermediate Similarity	NPD4518	Approved
0.7327	Intermediate Similarity	NPD7102	Approved
0.7327	Intermediate Similarity	NPD5247	Approved
0.7327	Intermediate Similarity	NPD5169	Approved
0.7327	Intermediate Similarity	NPD4634	Approved
0.7327	Intermediate Similarity	NPD5135	Approved
0.7327	Intermediate Similarity	NPD7290	Approved
0.7327	Intermediate Similarity	NPD5249	Phase 3
0.7327	Intermediate Similarity	NPD6883	Approved
0.7327	Intermediate Similarity	NPD5250	Approved
0.7327	Intermediate Similarity	NPD5248	Approved
0.7327	Intermediate Similarity	NPD5251	Approved
0.7327	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5091	Approved
0.7317	Intermediate Similarity	NPD6924	Approved
0.7317	Intermediate Similarity	NPD4785	Approved
0.7317	Intermediate Similarity	NPD4784	Approved
0.7317	Intermediate Similarity	NPD6926	Approved
0.73	Intermediate Similarity	NPD7320	Approved
0.7284	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5693	Phase 1
0.7263	Intermediate Similarity	NPD7902	Approved
0.7255	Intermediate Similarity	NPD5215	Approved
0.7255	Intermediate Similarity	NPD5127	Approved
0.7255	Intermediate Similarity	NPD5216	Approved
0.7255	Intermediate Similarity	NPD6650	Approved
0.7255	Intermediate Similarity	NPD8130	Phase 1
0.7255	Intermediate Similarity	NPD5217	Approved
0.7255	Intermediate Similarity	NPD6617	Approved
0.7255	Intermediate Similarity	NPD6869	Approved
0.7255	Intermediate Similarity	NPD6649	Approved
0.7255	Intermediate Similarity	NPD6847	Approved
0.7253	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6922	Approved
0.725	Intermediate Similarity	NPD3698	Phase 2
0.725	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6923	Approved
0.7241	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4190	Phase 3
0.7229	Intermediate Similarity	NPD5275	Approved
0.7228	Intermediate Similarity	NPD6373	Approved
0.7228	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD3573	Approved
0.72	Intermediate Similarity	NPD6412	Phase 2
0.7184	Intermediate Similarity	NPD8297	Approved
0.7184	Intermediate Similarity	NPD6882	Approved
0.7176	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5207	Approved
0.7174	Intermediate Similarity	NPD5692	Phase 3
0.716	Intermediate Similarity	NPD7144	Approved
0.716	Intermediate Similarity	NPD4245	Approved
0.716	Intermediate Similarity	NPD4244	Approved
0.716	Intermediate Similarity	NPD7143	Approved
0.7143	Intermediate Similarity	NPD6933	Approved
0.7128	Intermediate Similarity	NPD6001	Approved
0.7115	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD5694	Approved
0.7097	Intermediate Similarity	NPD6050	Approved
0.7093	Intermediate Similarity	NPD7645	Phase 2
0.7089	Intermediate Similarity	NPD7331	Phase 2
0.7089	Intermediate Similarity	NPD4224	Phase 2
0.7087	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7151	Approved
0.7073	Intermediate Similarity	NPD7152	Approved
0.7073	Intermediate Similarity	NPD7150	Approved
0.7048	Intermediate Similarity	NPD5167	Approved
0.7033	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5290	Discontinued
0.701	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD1696	Phase 3
0.6981	Remote Similarity	NPD6274	Approved
0.6981	Remote Similarity	NPD6868	Approved
0.6979	Remote Similarity	NPD7614	Phase 1
0.6966	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7900	Approved
0.6939	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD6404	Discontinued
0.6939	Remote Similarity	NPD7639	Approved
0.6916	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD7115	Discovery

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data